1762-41-0

Usage

Uses

Used in Coordination Chemistry:
4,4'-DICHLORO-2,2'-BIPYRIDINE is used as a ligand for the synthesis of metal complexes, leveraging its strong chelating and coordinating properties. This application is crucial in the field of catalysis, where metal complexes can act as catalysts to accelerate chemical reactions, and in molecular recognition, where the compound can selectively bind to specific molecules.
Used in Organic Synthesis:
As a building block in organic synthesis, 4,4'-DICHLORO-2,2'-BIPYRIDINE contributes to the development of new materials and functional molecules. Its chemical structure and reactivity are valuable for designing novel compounds with a range of applications in chemistry and material science.
Used in the Development of New Materials:
4,4'-DICHLORO-2,2'-BIPYRIDINE is utilized in the creation of new materials, where its unique properties can be harnessed to enhance the performance of these materials. Its role in this application is to provide structural and functional diversity, which can lead to advancements in various industries.
Used in Functional Molecule Design:
In the design of functional molecules, 4,4'-DICHLORO-2,2'-BIPYRIDINE serves as a key component that can impart specific properties to these molecules. Its inclusion in molecular structures can lead to the development of compounds with targeted applications in fields such as pharmaceuticals, agrochemicals, and other specialized chemical industries.

Upstream product

• 51595-55-2 4,4'-dinitro-2,2'-bipyridyl-N,N'-dioxide 
• 1003-09-4 2-bromothiophene 
• 139585-50-5 4-chloro-2-trimethylsilylpyridine 
• 99-90-1 para-bromoacetophenone 
• 22918-01-0 2-bromo-4-chloropyridine 
• 13534-89-9 2,3-dibromopyridine 
• 615-37-2 ortho-methylphenyl iodide 
• 84175-05-3 4'-nitro-2,2'-bipyridine-N-oxide 
• 455-13-0 4-Iodobenzotrifluoride 
• 626-55-1 3-Bromopyridine 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 366-18-7 [2,2]bipyridinyl 
• 84175-08-6 4,4’-dichloro-2,2’-bipyridine-N,N’-dioxide 

Downstream Products

• 5470-22-4 4-chloropicolinic acid 
• 18511-69-8 4,4'-diamino-2,2'-bipyridyl 
• 1189458-67-0 4,4'-difluoro-2,2'-bipyridine 
• 254450-33-4 4,4'-([2,2'-bipyridine]-4,4'-diyl)diphenol 
• 85698-56-2 N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine 
• 642932-88-5 trans-[(1,4-bis(diphenylphosphino)butane)(4,4'-dichloro-2,2'-bipyridine)dichlororuthenium(II)] 
• 204573-71-7 [Re(C(2,4,6-Me₃C₆H₂))(4,4'-dichloro-2,2'-bipyridine)(CO)2Cl]ClO₄ 
• 101028-40-4 2,2'-bipyridine-4(1H),4'(1'H)-dithione 
• 101028-38-0 4,4'-bis(methylthio)-2,2'-bipyridine 

Relevant academic research and scientific papers

Strongly blue luminescent cationic iridium(III) complexes with an electron-rich ancillary ligand: Evaluation of their optoelectronic and electrochemiluminescence properties

Two strongly blue luminescent cationic heteroleptic iridium complexes 1b and 2b bearing a 4,4′-bis(dimethylamino)-2,2′-bipyridine (dmabpy) ancillary ligand and either 1-benzyl-4-(2,4-difluorophenyl)-1H-1,2,3-triazole (dFphtl) or 2-(2,4-difluorophenyl)-5-methylpyridine (dFMeppyH), respectively, have been synthesized and fully characterized. In comparison with other analogues, the interplay of the triazole unit with the dmabpy unit and methylation of the pyridine ring are discussed with respect to the photophysical, electrochemical, and electrochemiluminescent (ECL) properties of the complexes. The two complexes, 1b and 2b, are blue emitters with λmax = 495 and 494 nm, respectively. The nature of the excited states was established by various photophysical and photochemical experiments as well as DFT calculations. Both complexes emit from a ligand-centered state, however, the emission of 1b possesses significant charge-transfer character, which is absent in 2b. The presence of the methyl group on the cyclometalating ligand leads only to a modest increase in the radiative rate constant, k r, but otherwise does not appreciably influence the optoelectronic properties of the complex compared with the non-methylated analogue. In contrast, the efficacy of the ECL emission when scanning to 2.50 V is strongly influenced by the presence of the methyl group. ECL emission is also enhanced in complexes bearing dmabpy ancillary ligands compared with those containing dtBubpy ligands. The two complexes exhibit similar electrochemical behavior. Incorporation of the dmabpy ligand shifts both the oxidation and reduction cathodically. The combination of the dmabpy and dFphtl groups increases the redox potential difference and thus the HOMO-LUMO gap but the emission is not further blueshifted. Thus, the structural modification of the cyclometalating ligand, although only modestly tuning the emission energy, modulates the nature of the excited state and the efficiency of the ECL process. The synthesis, photophysical, electrochemical, and electrochemiluminescent properties of two highly emissive cationic blue-emitting Ir complexes are reported. Variation of the ligand results in a change in the nature of the emission. The decoration on both the cyclometalating and ancillary ligands strongly influences the ECL efficiencies. A detailed DFT/TDDFT study corroborates experiment. Copyright

A NOVEL REARRANGEMENT OF 2,2'-BIPYRIDINE N,N'-DIOXIDES THE CHARACTERISATION OF DIPYRIDO ISOXAZOLINIUM SALTS AS INTERMEDIATES IN THE FORMATION OF 3-HYDROXY-2,2'-BIPYRIDINES

The reactions of 2,2'-bipyridine N,N'-dioxides with POCl3 and SO2Cl2 have been investigated, and the products shown to be synthetically useful halogenated derivatives.The presence of substituents in the 4 position favours an intramolecular cyclisation to form dipyrido-isoxazolinium salts, which have been characterised for the first time.

Novel di- and tetra(pyrazolyl)bipyridine ligands and their Co (II)-complexes for electrochemical applications

Novel di- and tetra(pyrazolyl)bipyridine ligands have been prepared from available bipyridine N-oxide and N,N′-dioxide nitro derivatives via nucleophilic substitution reactions. The ligands were converted to the corresponding homoleptic octahedral cobalt

Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A

Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.

Electronic effects on reactivity and anticancer activity by half-sandwich N,N-chelated iridium(iii) complexes

The synthesis and characterization of a series of organometallic half-sandwich N,N-chelated iridium(iii) complexes bearing a range of electron-donating and withdrawing substituents were described. The X-ray crystal structures of complexes 1, 3 and 5 have been determined. This work demonstrated how the aqueous chemistry, catalytic activity in converting coenzyme NADH to NAD+ and anticancer activity can be controlled and fine-tuned by the modification of the ligand electronic perturbations. In general, the introduction of an electron-withdrawing group (-Cl and-NO2) on the bipyridine ring resulted in increased anticancer activity, whereas an electron-donating group (-NH2,-OH and-OCH3) decreased the anticancer activity. Complex 6 bearing a strongly electron-withdrawing NO2 group displayed the highest anticancer activity (7.3 ± 1.2 μM), ca. three times as active as cisplatin in the A549 cell line. Notably, selective cytotoxicity for cancer cells over normal cells was observed for complexes 1 and 6. DNA binding does not seem to be the primary mechanism for cancer fighting. However, the aqueous chemistry, cell apoptosis and cell cycle, which show similar dependence on the ligand electronic perturbations as the anticancer activity, appear to together contribute to the anticancer potency of theses complexes. This work may provide an alternative strategy to enhance anticancer activity for these N,N-chelated organometallic half-sandwich iridium(iii) complexes.

Isomer Dependence of Efficiency and Charge Recombination in Dye-Sensitized Solar Cells Using Ru Complex Dyes Bearing Halogen Substituents

We have synthesised Ru(H2-dcbpy)(N,N′-Y2-bpy)(NCS)2 dyes (where N = 4, 5; Y = F, Cl, Br; N is the position on the bipyridyl ring where the halogen substituent is located) for dye-sensitised solar cells. We show that careful consideration of the position of the substituent, in conjunction with the nature of the substituents, on a bpy ring is important to optimize the solar cells performance. Changing the position (from 4,4′ to 5,5′) along with the nature of the halogen (F, Cl, or Br) substituents were observed to cause changes in the electronic and spectroscopic properties of the dyes as well as influence the recombination rates at the TiO2-dyes-I-/I3- interface affecting the performance of the dyes in DSSCs. Changing the position (from 4,4′ to 5,5′) along with the nature of the halogen (F, Cl, or Br) substituents affects the electronic and spectroscopic properties of the Ru(H2-dcbpy)(N,N′-Y2-bpy)(NCS)2 dyes as well as the recombination rates at the TiO2-dyes-I-/I3- interface hence affecting the performance of the dyes in DSSCs.

TBAF-Catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: Access to arylpyridines and bihetaryl compounds

The concomitant use of silver oxide and catalytic amount of TBAF allowed the efficient and chemoselective coupling of readily available 4-chloro- and 4-methyl-2-trimethyl-silyl-pyridines with heteroaromatic and aromatic halides. Based on control experiments, a mechanism involving the formation of a pyridylsilver intermediate and TBAF recycling is postulated.

Conversion of solar energy to chemical energy

The rate of evolution of hydrogen from water by photochemical process using solar energy has been investigated employing fourteen metal complexes as catalysts, ten electron relays, three electron donors and two co-catalysts in different permutation and combinations. The effect of varying reaction conditions like temperature, concentration and pH have also been investigated for the optimum production of hydrogen by the photochemical cleavage of water molecules.

Functional polypyridine ligands from copper-mediated room temperature coupling of 4-chloro-2-trimethylsilylpyridine

A range of functional polypyridine ligands (bipyridines and terpyridine) has been synthesized by copper-mediated oxidative homocoupling of 4-chloro-2-trimethylsilylpyridine or cross-coupling with functional bromopyridines. The reaction proceeded smoothly at room temperature.

Synthesis of 2,4-dibromopyridine and 4,4'-dibromo-2,2'-bipyridine. Efficient usage in selective bromine-substitution under palladium-catalysis

We report an efficient method for preparing 2,4-dibromopyridine and 4,4'-dibromo-2,2'-bipyridine from the corresponding nitroazine N-oxide in one step via a tandem nucleophilic substitution-N-oxide reduction process. The one step preparation of 4,4'-dihalo-2,2'-bipyridines from dihalopyridines via a Stille reaction is also described. 4,4'-Dibromo-2,2'-bipyridine undergoes selective mono- or disubstitution processes under palladium catalysis. This short synthetic procedure is an efficient and reliable process for preparing conjugated pyridine and 2,2'-bipyridine building blocks for applications in coordination chemistry and materials science.